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Credit to my colleague Chuck Drake for this one…but How Do You Eat an Elephant? One Bite at a Time. The David Allen school of time management (post, book) talks about breaking your projects down into “Next Actions” so they don’t become overwhelming and can easily move forward one step at a time.

I think the same is true of organizational projects – perhaps even more so. Any time we find ourselves swirling around a big initiative at Return Path, we are at our best when we ask ourselves some questions along these lines:

How can we be scrappier about this?

It it ok to be messy here…or at least not perfect?

What is the next milestone?

What else needs to be done until we learn the likely outcome?

We had a great example of this recently around rolling out a new product to our sales and service team. The team is now pretty large – over 100 globally. It was a daunting task to try to get all those people trained up at once. The answer? We took a bite out of the elephant. We picked a couple of sales reps and a couple of account managers and started by training them on the new product. Now we can figure out how to institutionalize learnings from the limited roll-out and figure out the next step from there. Much easier than what otherwise would have been a pretty high-stakes project without enough learnings behind it, even though it will take a little longer and be a little messier.